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The Chester Opera House was built in the late 19th century. It was converted to a movie house about 1920 by its owner, Bill Schuchert. Elzie Segar, the creator of Popeye the Sailor, a native of Chester, got his first job at the Opera House working for Schuchert at age 12. Segar would later base the hamburger-loving character of Wimpy on his former boss.

Though long ago closed as a movie theater, the old Opera House now houses a Popeye-themed gift shop and museum.

The Opera House in Chester IL was listed in the 1897-98 edition of the Julius Cahn Official Theatrical Guide, an annual for roadshow managers. Its seating capacity was given as 650. It was under the managment of Herman Wiebusch and Edw. Tindall. Ticket prices ranged from 25 cents to 50 cents. The proscenium opening was 18 feet wide x 9 feet high, and the stage was 18 feet deep. The theatre was on the second floor and had electric illumination. There apparently were no less than 7 hotels in Chester, and 3 newspapers. The town was served by 2 railroads and 3 steamboat lines. The population was 5,000.